6 Tips for Keeping Conversation Flowing on a First Date

Some things in life really never get any easier, no matter how confident or successful a sugardaddy might be. One of them is keeping a sparkling stream of conversation flowing when he’s out on a date, as the art of conversation doesn’t come naturally to everyone. Maybe this particular would-be sugar baby is shy (or you are). Perhaps she’s just someone you feel extra attracted to and wants to make sure to impress.

And then there are the times when an awkward silence presents itself for no real reason. Whatever the case may be, it always helps to have a few tips, tricks, and conversation topics in your back pocket, just in case they’re needed. Here are a few every sugardaddy should keep in mind.

1.      Pay her a compliment

Every sugar baby likes to know her date has noticed how much effort she put into her look for the evening, so it’s pretty hard to go wrong by paying your date a compliment. Hopefully, it should be a tasteful compliment (so no weird commentary on her banging body).

But you want to make sure it’s not a dull or boring one, either, so avoid the standard “you look great” approach if you can help it. Find something specific but appropriate to mention – like her gorgeous hairstyle or a piece of statement jewelry she has on.

2.      Comment on the setting

When you’re at a loss for something to say, it’s usually pretty easy to find inspiration in your immediate surroundings. Take a quick glance around the restaurant or venue where you are. Find something interesting or noteworthy, and bring it up for discussion.

For example, the food or ambiance are always good choices if you’re at a restaurant. But you can also share a story about why you like this particular place or the food here. Just steer clear of commenting on other people who might be around, as this can come across as gossipy and inappropriate.

3.      Give thoughtful answers to questions

Unless this particular sugar baby is extremely shy or nervous, she’s almost certainly doing her part to keep the conversation flowing. She’s likely making her own comments, telling stories, and asking you questions about yourself. Make things easy on her, and be sure to give thorough answers that are well thought out.

Take advantage of opportunities to tell her interesting details about yourself related to her original question. Then ask her similar questions and listen attentively to the answers. Great conversation on a first date is all about actively listening and reacting to one another, and this is a great way to get that dynamic going.

4.      Touch on career and life goals

Most sugar babies are like the sugardaddies they date – extremely goal-oriented, passionate, and driven about the things they want to accomplish in life. And pretty much everyone comes alive when given the opportunity to discuss their passions with someone who genuinely wants to hear it.

Is this sugar baby working or going to school? Ask her to tell you more about her goals and related interests. Has she mentioned any particular hobbies or other topics in any of your online interactions? Ask about those, and offer any relevant information about yourself that might demonstrate a deeper potential connection between the two of you.

5.      Approach the family topic with cautio1n

Family is the type of topic that can either be a great conversation booster or a total landmine. It depends on the other person’s unique background and feelings about it. If you don’t already know which side of the equation your date falls on, casually ask whether she’s close with her parents or her family, and let her take it from there.

She’ll tell you if this is a sensitive topic or outright say she and her family aren’t close. And if she does, drop the topic instead of probing further to satisfy your curiosity. Not everyone had a terrific childhood or wonderful parents, and sometimes even those who did prefer to save that topic for another time.

6.      Don’t shy away from deal-breakers

For most sugardaddies and beautiful sugar babies, it’s pretty customary to start talking about potential relationship deal-breakers as soon as it’s established that there’s a connection there. So if you feel like you’ve picked up on such a connection, this could be a great way to keep the conversation going in a meaningful way.

If it’s important to be with someone who wants kids or shares certain values, interests, and beliefs, now is the time to bring it up. Encourage your date to do the same. Most sugar daters like to cut straight to the chase, so the sooner you find out whether you’re potentially compatible over the long term, the better.




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It's a little lonely being one of the two female writers here, but I do my best! You'll find me covering everything from relationships to the newest gadget I'm excited about.

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